NPASS Compound

Structure

NPC104956 OpenBabel07101718292D 33 36 0 0 1 0 0 0 0 0999 V2000 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.4055 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0754 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.4055 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5395 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9414 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9414 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 16.5395 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8075 -1.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6735 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6735 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5395 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.8075 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.8075 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 21 1 0 0 0 0 14 23 1 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 25 1 0 0 0 0 18 21 2 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 31 1 0 0 0 0 20 32 1 0 0 0 0 22 13 1 6 0 0 0 22 33 1 0 0 0 0 23 28 1 0 0 0 0 23 29 2 0 0 0 0 24 28 1 0 0 0 0 24 30 1 6 0 0 0 25 27 2 0 0 0 0 25 31 1 0 0 0 0 26 28 2 0 0 0 0 26 33 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.29
Volume:	489.387
LogP:	7.294
LogD:	4.417
LogS:	-6.556
# Rotatable Bonds:	13
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	3.828
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.96
MDCK Permeability:	3.838645352516323e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.102
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	97.46186065673828%
Volume Distribution (VD):	1.451
Pgp-substrate:	0.914770245552063%

ADMET: Metabolism

CYP1A2-inhibitor:	0.327
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.801
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.39
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.98
CYP2D6-substrate:	0.457
CYP3A4-inhibitor:	0.977
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	10.935
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.626
Human Hepatotoxicity (H-HT):	0.561
Drug-inuced Liver Injury (DILI):	0.172
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.952
Carcinogencity:	0.396
Eye Corrosion:	0.006
Eye Irritation:	0.078
Respiratory Toxicity:	0.9

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC104956

Natural Product ID:	NPC104956
*Common Name:**	(2S,4R)-2-[12-(1,3-Benzodioxol-5-Yl)Dodecyl]-4-Hydroxy-2,3,4,6,7,8-Hexahydrochromen-5-One
IUPAC Name:	(2S,4R)-2-[12-(1,3-benzodioxol-5-yl)dodecyl]-4-hydroxy-2,3,4,6,7,8-hexahydrochromen-5-one
Synonyms:
Standard InCHIKey:	YHJGSFFBACPLMU-LADGPHEKSA-N
Standard InCHI:	InChI=1S/C28H40O5/c29-23-14-11-15-26-28(23)24(30)19-22(33-26)13-10-8-6-4-2-1-3-5-7-9-12-21-16-17-25-27(18-21)32-20-31-25/h16-18,22,24,30H,1-15,19-20H2/t22-,24+/m0/s1
SMILES:	C(CCCCCC[C@H]1C[C@H](C2=C(CCCC2=O)O1)O)CCCCCc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL427288
PubChem CID:	16737474
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499322]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17358082]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17547458]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[503856]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[503856]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	18.2	ug.mL-1	PMID[503856]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	65.2	ug.mL-1	PMID[503856]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	48.8	ug.mL-1	PMID[503856]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC104956 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	1304
0.2-0.3	3111
0.3-0.4	7489
0.4-0.5	11268
0.5-0.6	4205
0.6-0.7	8864
0.7-0.8	5995
0.8-0.85	108
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9111	High Similarity	NPC477706
0.9037	High Similarity	NPC477694
0.9037	High Similarity	NPC477705
0.9	High Similarity	NPC470855
0.869	High Similarity	NPC327052
0.8571	High Similarity	NPC476336
0.8542	High Similarity	NPC28398
0.8542	High Similarity	NPC51681
0.8523	High Similarity	NPC12854
0.8519	High Similarity	NPC244876
0.8493	Intermediate Similarity	NPC15743
0.8478	Intermediate Similarity	NPC278308
0.8477	Intermediate Similarity	NPC35544
0.8477	Intermediate Similarity	NPC104728
0.8442	Intermediate Similarity	NPC469384
0.8421	Intermediate Similarity	NPC476364
0.8406	Intermediate Similarity	NPC20404
0.8406	Intermediate Similarity	NPC20287
0.8406	Intermediate Similarity	NPC293641
0.8406	Intermediate Similarity	NPC12022
0.8397	Intermediate Similarity	NPC125991
0.8394	Intermediate Similarity	NPC85830
0.8387	Intermediate Similarity	NPC218471
0.8387	Intermediate Similarity	NPC239818
0.838	Intermediate Similarity	NPC471110
0.8378	Intermediate Similarity	NPC30890
0.8377	Intermediate Similarity	NPC475663
0.8377	Intermediate Similarity	NPC286919
0.8367	Intermediate Similarity	NPC46880
0.8366	Intermediate Similarity	NPC131532
0.8357	Intermediate Similarity	NPC137427
0.8357	Intermediate Similarity	NPC65935
0.8357	Intermediate Similarity	NPC244246
0.8357	Intermediate Similarity	NPC311419
0.8357	Intermediate Similarity	NPC123196
0.8357	Intermediate Similarity	NPC215941
0.8357	Intermediate Similarity	NPC319282
0.8357	Intermediate Similarity	NPC275724
0.8345	Intermediate Similarity	NPC474784
0.8344	Intermediate Similarity	NPC234152
0.8323	Intermediate Similarity	NPC179914
0.8323	Intermediate Similarity	NPC76211
0.8322	Intermediate Similarity	NPC153620
0.8322	Intermediate Similarity	NPC24257
0.8322	Intermediate Similarity	NPC88345
0.8291	Intermediate Similarity	NPC475738
0.8273	Intermediate Similarity	NPC64948
0.8269	Intermediate Similarity	NPC476337
0.8267	Intermediate Similarity	NPC116229
0.8258	Intermediate Similarity	NPC226759
0.8255	Intermediate Similarity	NPC189054
0.8255	Intermediate Similarity	NPC472560
0.8255	Intermediate Similarity	NPC3982
0.8239	Intermediate Similarity	NPC254306
0.8235	Intermediate Similarity	NPC44730
0.8235	Intermediate Similarity	NPC68882
0.8231	Intermediate Similarity	NPC52664
0.8217	Intermediate Similarity	NPC94155
0.8212	Intermediate Similarity	NPC478242
0.8207	Intermediate Similarity	NPC52968
0.8207	Intermediate Similarity	NPC231719
0.8207	Intermediate Similarity	NPC166184
0.8205	Intermediate Similarity	NPC215375
0.8205	Intermediate Similarity	NPC62518
0.82	Intermediate Similarity	NPC25496
0.8182	Intermediate Similarity	NPC475468
0.8182	Intermediate Similarity	NPC327410
0.8176	Intermediate Similarity	NPC180586
0.8175	Intermediate Similarity	NPC256167
0.817	Intermediate Similarity	NPC56184
0.817	Intermediate Similarity	NPC151425
0.8163	Intermediate Similarity	NPC282291
0.8163	Intermediate Similarity	NPC166137
0.8158	Intermediate Similarity	NPC158635
0.8158	Intermediate Similarity	NPC229882
0.8158	Intermediate Similarity	NPC205054
0.8158	Intermediate Similarity	NPC37220
0.8153	Intermediate Similarity	NPC225624
0.8153	Intermediate Similarity	NPC285973
0.8148	Intermediate Similarity	NPC261254
0.8148	Intermediate Similarity	NPC235575
0.8143	Intermediate Similarity	NPC286683
0.8141	Intermediate Similarity	NPC167595
0.8141	Intermediate Similarity	NPC220462
0.8138	Intermediate Similarity	NPC102260
0.8138	Intermediate Similarity	NPC230968
0.8138	Intermediate Similarity	NPC90431
0.8129	Intermediate Similarity	NPC10205
0.8125	Intermediate Similarity	NPC67037
0.8125	Intermediate Similarity	NPC255615
0.8117	Intermediate Similarity	NPC299706
0.8117	Intermediate Similarity	NPC61604
0.8117	Intermediate Similarity	NPC115466
0.8117	Intermediate Similarity	NPC245615
0.8117	Intermediate Similarity	NPC137813
0.8117	Intermediate Similarity	NPC308555
0.8113	Intermediate Similarity	NPC191306
0.8113	Intermediate Similarity	NPC270335
0.8113	Intermediate Similarity	NPC470178
0.8113	Intermediate Similarity	NPC88023
0.8113	Intermediate Similarity	NPC100425
0.8113	Intermediate Similarity	NPC309025
0.8113	Intermediate Similarity	NPC243930
0.8112	Intermediate Similarity	NPC50763
0.8105	Intermediate Similarity	NPC62354
0.8102	Intermediate Similarity	NPC193484
0.8101	Intermediate Similarity	NPC295009
0.8101	Intermediate Similarity	NPC182045
0.8101	Intermediate Similarity	NPC260640
0.8099	Intermediate Similarity	NPC172673
0.8099	Intermediate Similarity	NPC195292
0.8098	Intermediate Similarity	NPC105137
0.8089	Intermediate Similarity	NPC469654
0.8086	Intermediate Similarity	NPC212748
0.8079	Intermediate Similarity	NPC476338
0.8079	Intermediate Similarity	NPC476359
0.8077	Intermediate Similarity	NPC155063
0.8077	Intermediate Similarity	NPC471405
0.8077	Intermediate Similarity	NPC478055
0.8075	Intermediate Similarity	NPC229729
0.8075	Intermediate Similarity	NPC42892
0.8071	Intermediate Similarity	NPC303680
0.8071	Intermediate Similarity	NPC90128
0.8071	Intermediate Similarity	NPC84076
0.8069	Intermediate Similarity	NPC180171
0.8069	Intermediate Similarity	NPC174191
0.8069	Intermediate Similarity	NPC158325
0.8069	Intermediate Similarity	NPC103398
0.8065	Intermediate Similarity	NPC478213
0.8065	Intermediate Similarity	NPC25127
0.8063	Intermediate Similarity	NPC284277
0.8063	Intermediate Similarity	NPC22832
0.8063	Intermediate Similarity	NPC475366
0.8063	Intermediate Similarity	NPC475497
0.8063	Intermediate Similarity	NPC311830
0.8063	Intermediate Similarity	NPC165720
0.8063	Intermediate Similarity	NPC34531
0.8058	Intermediate Similarity	NPC273686
0.8058	Intermediate Similarity	NPC312404
0.8056	Intermediate Similarity	NPC205915
0.8054	Intermediate Similarity	NPC137920
0.8054	Intermediate Similarity	NPC125134
0.8054	Intermediate Similarity	NPC86455
0.8054	Intermediate Similarity	NPC472564
0.8052	Intermediate Similarity	NPC289438
0.8052	Intermediate Similarity	NPC134905
0.8052	Intermediate Similarity	NPC203664
0.8052	Intermediate Similarity	NPC36130
0.805	Intermediate Similarity	NPC476244
0.805	Intermediate Similarity	NPC127782
0.805	Intermediate Similarity	NPC300537
0.805	Intermediate Similarity	NPC148273
0.805	Intermediate Similarity	NPC189142
0.805	Intermediate Similarity	NPC77660
0.8049	Intermediate Similarity	NPC472607
0.8042	Intermediate Similarity	NPC469480
0.8041	Intermediate Similarity	NPC323601
0.8041	Intermediate Similarity	NPC100675
0.8039	Intermediate Similarity	NPC227980
0.8039	Intermediate Similarity	NPC475170
0.8038	Intermediate Similarity	NPC269906
0.8038	Intermediate Similarity	NPC110349
0.8028	Intermediate Similarity	NPC304622
0.8027	Intermediate Similarity	NPC284409
0.8026	Intermediate Similarity	NPC98009
0.8026	Intermediate Similarity	NPC473138
0.8026	Intermediate Similarity	NPC28776
0.8026	Intermediate Similarity	NPC1580
0.8025	Intermediate Similarity	NPC195257
0.8025	Intermediate Similarity	NPC293629
0.8025	Intermediate Similarity	NPC209296
0.8025	Intermediate Similarity	NPC223335
0.8025	Intermediate Similarity	NPC40920
0.8025	Intermediate Similarity	NPC86008
0.8014	Intermediate Similarity	NPC276466
0.8014	Intermediate Similarity	NPC324929
0.8014	Intermediate Similarity	NPC123722
0.8014	Intermediate Similarity	NPC151167
0.8014	Intermediate Similarity	NPC123228
0.8014	Intermediate Similarity	NPC5018
0.8013	Intermediate Similarity	NPC296575
0.8013	Intermediate Similarity	NPC254163
0.8013	Intermediate Similarity	NPC186316
0.8013	Intermediate Similarity	NPC38699
0.8012	Intermediate Similarity	NPC5778
0.8012	Intermediate Similarity	NPC21100
0.8012	Intermediate Similarity	NPC476277
0.8012	Intermediate Similarity	NPC197285
0.8012	Intermediate Similarity	NPC236934
0.8	Intermediate Similarity	NPC45404
0.8	Intermediate Similarity	NPC148497
0.8	Intermediate Similarity	NPC222936
0.8	Intermediate Similarity	NPC284960
0.8	Intermediate Similarity	NPC94777
0.8	Intermediate Similarity	NPC46161
0.8	Intermediate Similarity	NPC280767
0.8	Intermediate Similarity	NPC176814
0.8	Intermediate Similarity	NPC300776
0.8	Intermediate Similarity	NPC257589
0.8	Intermediate Similarity	NPC19890

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC104956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	816
0.2-0.3	1688
0.3-0.4	2555
0.4-0.5	2035
0.5-0.6	1095
0.6-0.7	578
0.7-0.8	88
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8435	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD3818	Discontinued
0.8025	Intermediate Similarity	NPD7054	Approved
0.7975	Intermediate Similarity	NPD7472	Approved
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7908	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1357	Approved
0.7871	Intermediate Similarity	NPD7028	Phase 2
0.7831	Intermediate Similarity	NPD7808	Phase 3
0.7799	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1934	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD37	Approved
0.7736	Intermediate Similarity	NPD4965	Approved
0.7736	Intermediate Similarity	NPD4966	Approved
0.7736	Intermediate Similarity	NPD4967	Phase 2
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6797	Phase 2
0.7654	Intermediate Similarity	NPD7199	Phase 2
0.7625	Intermediate Similarity	NPD3882	Suspended
0.761	Intermediate Similarity	NPD2801	Approved
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3817	Phase 2
0.756	Intermediate Similarity	NPD7685	Pre-registration
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.7531	Intermediate Similarity	NPD6234	Discontinued
0.7517	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD4110	Phase 3
0.7516	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1511	Approved
0.7482	Intermediate Similarity	NPD5536	Phase 2
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7465	Intermediate Similarity	NPD3705	Approved
0.7455	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7266	Discontinued
0.7425	Intermediate Similarity	NPD7228	Approved
0.7417	Intermediate Similarity	NPD7033	Discontinued
0.7417	Intermediate Similarity	NPD1510	Phase 2
0.7405	Intermediate Similarity	NPD1653	Approved
0.7403	Intermediate Similarity	NPD4628	Phase 3
0.7389	Intermediate Similarity	NPD1512	Approved
0.7378	Intermediate Similarity	NPD5494	Approved
0.7355	Intermediate Similarity	NPD6190	Approved
0.7353	Intermediate Similarity	NPD6559	Discontinued
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD1933	Approved
0.7333	Intermediate Similarity	NPD447	Suspended
0.7329	Intermediate Similarity	NPD2798	Approved
0.7321	Intermediate Similarity	NPD3751	Discontinued
0.732	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3027	Phase 3
0.729	Intermediate Similarity	NPD8166	Discontinued
0.7284	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7262	Intermediate Similarity	NPD7473	Discontinued
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7075	Discontinued
0.7255	Intermediate Similarity	NPD2935	Discontinued
0.7255	Intermediate Similarity	NPD2796	Approved
0.7248	Intermediate Similarity	NPD3268	Approved
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7229	Intermediate Similarity	NPD8127	Discontinued
0.7222	Intermediate Similarity	NPD6801	Discontinued
0.7215	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD919	Approved
0.7211	Intermediate Similarity	NPD5647	Approved
0.72	Intermediate Similarity	NPD6233	Phase 2
0.7194	Intermediate Similarity	NPD5283	Phase 1
0.7194	Intermediate Similarity	NPD1241	Discontinued
0.7186	Intermediate Similarity	NPD6232	Discontinued
0.7186	Intermediate Similarity	NPD3787	Discontinued
0.7179	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7819	Suspended
0.7176	Intermediate Similarity	NPD5844	Phase 1
0.7174	Intermediate Similarity	NPD228	Approved
0.7171	Intermediate Similarity	NPD6653	Approved
0.7161	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7133	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6674	Discontinued
0.7107	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2344	Approved
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.7067	Intermediate Similarity	NPD7095	Approved
0.7051	Intermediate Similarity	NPD2424	Discontinued
0.7044	Intermediate Similarity	NPD6799	Approved
0.7039	Intermediate Similarity	NPD1613	Approved
0.7039	Intermediate Similarity	NPD3620	Phase 2
0.7039	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1240	Approved
0.7037	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5402	Approved
0.7024	Intermediate Similarity	NPD1247	Approved
0.702	Intermediate Similarity	NPD2313	Discontinued
0.7019	Intermediate Similarity	NPD5403	Approved
0.7013	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD2533	Approved
0.7	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD2532	Approved
0.7	Intermediate Similarity	NPD7843	Approved
0.6994	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD230	Phase 1
0.6986	Remote Similarity	NPD1091	Approved
0.6986	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4062	Phase 3
0.6972	Remote Similarity	NPD7157	Approved
0.6971	Remote Similarity	NPD8312	Approved
0.6971	Remote Similarity	NPD8313	Approved
0.697	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2799	Discontinued
0.6962	Remote Similarity	NPD3750	Approved
0.6957	Remote Similarity	NPD2684	Approved
0.6957	Remote Similarity	NPD6273	Approved
0.6951	Remote Similarity	NPD6385	Approved
0.6951	Remote Similarity	NPD6386	Approved
0.6951	Remote Similarity	NPD7411	Suspended
0.6949	Remote Similarity	NPD8434	Phase 2
0.6948	Remote Similarity	NPD1607	Approved
0.6948	Remote Similarity	NPD2492	Phase 1
0.6944	Remote Similarity	NPD1894	Discontinued
0.6941	Remote Similarity	NPD3926	Phase 2
0.6939	Remote Similarity	NPD3972	Approved
0.6939	Remote Similarity	NPD1608	Approved
0.6932	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD943	Approved
0.6923	Remote Similarity	NPD2438	Suspended
0.6918	Remote Similarity	NPD2309	Approved
0.6913	Remote Similarity	NPD3266	Approved
0.6913	Remote Similarity	NPD3267	Approved
0.6897	Remote Similarity	NPD1651	Approved
0.6894	Remote Similarity	NPD5401	Approved
0.6894	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6599	Discontinued
0.6887	Remote Similarity	NPD6832	Phase 2
0.6884	Remote Similarity	NPD1358	Approved
0.6875	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8032	Phase 2
0.6855	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4626	Approved
0.6846	Remote Similarity	NPD1283	Approved
0.6846	Remote Similarity	NPD3225	Approved
0.6835	Remote Similarity	NPD5958	Discontinued
0.6829	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD9545	Approved
0.6826	Remote Similarity	NPD5353	Approved
0.6824	Remote Similarity	NPD9717	Approved
0.6818	Remote Similarity	NPD4140	Approved
0.6818	Remote Similarity	NPD4060	Phase 1
0.6815	Remote Similarity	NPD6099	Approved
0.6815	Remote Similarity	NPD6100	Approved
0.6813	Remote Similarity	NPD3887	Approved
0.6807	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6844	Discontinued
0.6803	Remote Similarity	NPD3496	Discontinued
0.6803	Remote Similarity	NPD3847	Discontinued
0.68	Remote Similarity	NPD1203	Approved
0.6797	Remote Similarity	NPD3764	Approved
0.6792	Remote Similarity	NPD4237	Approved
0.6792	Remote Similarity	NPD4236	Phase 3
0.6792	Remote Similarity	NPD2800	Approved
0.679	Remote Similarity	NPD3146	Approved
0.679	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5691	Approved
0.6778	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6002	Phase 3
0.6772	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6004	Phase 3
0.6772	Remote Similarity	NPD6005	Phase 3
0.6772	Remote Similarity	NPD2346	Discontinued
0.6772	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5058	Phase 3
0.677	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2977	Approved
0.6766	Remote Similarity	NPD2978	Approved
0.6766	Remote Similarity	NPD1465	Phase 2
0.6766	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1535	Discovery
0.6753	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6663	Approved
0.6752	Remote Similarity	NPD3748	Approved
0.6752	Remote Similarity	NPD4308	Phase 3
0.675	Remote Similarity	NPD6331	Phase 2
0.6746	Remote Similarity	NPD3749	Approved
0.6735	Remote Similarity	NPD2932	Approved
0.6735	Remote Similarity	NPD17	Approved
0.6735	Remote Similarity	NPD1778	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data